Lithium Hydroxide → 5-Bromo-2-[(3-chlorophenyl)methoxy]benzoic acid
Reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[C:8]([CH:20]=1)[C:9]([O:11]CC1C=CC=C(Cl)C=1)=[O:10]>O.C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)=[C:8]([CH:20]=1)[C:9]([OH:11])=[O:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of lithium hydroxide (384 mg, 9.16 mmol) in water (20 ml) was added dropwise to a stirred solution of (3-chlorophenyl)methyl 5-bromo-2-([(3-chlorophenyl)methyl]oxy)benzoate (may be prepared as described in Description 21; 427 mg, 0.92 mmol) in THF (20 ml) over 1 min. The reaction mixture was stirred at 20° C. for 16 h. The organic phase was evaporated and the aqueous phase (20 ml) was extracted with ethyl acetate (20 ml). The aqueous phase (20 ml) was adjusted to pH 2 with 2M hydrochloric acid (1 ml). The aqueous phase was then extracted with ethyl acetate (3×20 ml). The organic phase was evaporated in vacuo to yield the title compound as a white solid. 200 mg.
Workup
- customThe organic phase was evaporated
- extractionthe aqueous phase (20 ml) was extracted with ethyl acetate (20 ml)
- extractionThe aqueous phase was then extracted with ethyl acetate (3×20 ml)
- customThe organic phase was evaporated in vacuo
Sources & evidence
- ORD record
- ord-1ac51b3ff8e94f67bdfa2c4b6fdaf25f
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778939B2
Reaction notes
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